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Piperidine-triazine compounds for use as stabilizers for organic materials

  • US 5,047,531 A
  • Filed: 08/02/1989
  • Issued: 09/10/1991
  • Est. Priority Date: 08/04/1988
  • Status: Expired due to Fees
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1. A compound of formula I ##STR59## in which R1 is hydrogen, C1 -C8 alkyl, 0°

  • , OH, NO, CH2 CN, C1 -C18 alkoxy, C5 -C12 cycloalkoxy, C3 -C6 alkenyl, C7 -C9 phenylalkyl which is unsubstituted or mono, di-or tri-substituted on the phenyl by C1 -C4 alkyl, C1 -C8 -acyl or C2 -C4 alkyl substituted in the 2-, 3- or 4-position by OH;

    R2 is C2 -C12 alkylene;

    R3 is a group of formula II ##STR60## with R1 and R2 being as defined above, or R3 is a group --OR4, --SR4 or ##STR61## in which R4 is C1 -C18 alkyl, C5 -C12 cycloalkyl which is unsubstituted or mono-, di- or tri-substituted by C1 -C4 alkyl, C3 -C18 alkenyl, phenyl which is unsubstituted or mono, di- or tri-substituted by C1 -C4 alkyl, C7 -C9 -phenylalkyl which is unsubstituted or mono, di- or tri-substituted on the phenyl by C1 -C4 alkyl, or a group of the formula (III) ##STR62## where R7 has any of the meanings given for R1 ;

    R5 and R6 which can be identical or different are hydrogen, C1 -C18 alkyl, C5 -C12 cycloalkyl which is unsubstituted or mono, di- or tri-substituted by C1 -C4 alkyl, C7 -C9 -phenylalkyl which is unsubstituted or mono-, di- or tri-substituted on the phenyl by C1 -C4 alkyl, C2 -C4 alkyl substituted in the 2-, 3- or 4-position by OH, by C1 -C8 alkoxy or by di-(C1 -C4 alkyl)-amino, C3 -C18 -alkenyl, tetrahydrofurfuryl or a group of the formula (III), or R5 and R6, together with the nitrogen atom to which they are linked, form part of a 5-membered to 7-membered heterocyclic ring which is 1 -pyrrolidyl, 1-piperidyl, 4-morpholinyl, 4-methyl-1-piperazinyl, 1-hexahydroazepinyl, 5,5,7-trimethyl-1-homopiperazinyl or 4,5,5,7-tetramethyl-1-homopiperazinyl; and

    w is an integer from 2 to 6; and

    when w is 2,A is one of the groups of the formula (IVa)-(IVd) ##STR63## in which R8 is C2 -C12 alkylene, cyclohexylene, cyclohexylenedimethylene, methylenedicyclohexylene, (C2 -C6 alkylidene)-dicyclohexylene, phenylene, (C2 -C6 alkylidene)-diphenylene, xylylene or C4 -C12 alkylene interrupted by 1, 2 or 3 oxygen atoms;

    R9 and R11 which can be identical or different are hydrogen, C1 -C18 alkyl, C5 -C12 cycloalkyl which is unsubstituted or mono-, di- or tri-substituted by C1 -C4 alkyl, C7 -C9 phenylalkyl which is unsubstituted or mono-, di- or tri-substituted on the phenyl by C1 -C4 -alkyl, or a group of the formula (III);

    R10 is as defined above for R8 or C4 -C12 alkylene interrupted by 1 or 2 groups ##STR64## where R15 has any of the meanings given above for R9 and R11, or is one of the groups of the formula (Va)-Vd) ##STR65## where R16 is hydrogen, C1 -C18 alkyl, C5 -C12 cycloalkyl which is unsubstituted or mono, di- or tri-substituted by C1 -C4 alkyl, C2 -C18 alkenyl, phenyl which is unsubstituted or mono-, di- or tri-substituted by C1 -C4 -alkyl or an OH group or mixture thereof, C7 -C9 phenylalkyl which is unsubstituted or mono-, di-or tri-substituted on the phenyl by C1 -C4 alkyl or an OH group or mixture thereof;

    R17 is C1 -C18 alkyl, C5 -C12 cycloalkyl which is unsubstituted or mono-, di- or tri-substitutedc by C1 -C4 alkyl, C3 -C18 alkenyl or a group of the formula (III);

    R18 is C1 -C18 alkyl or phenyl which is unsubstituted or mono-, di- or tri-substituted by C1 -C4 alkyl;

    m is zero or 1;

    R12 is hydrogen or methyl;

    n is zero, 1, 2, 3 or 4;

    R13 and R14 which are identical or different are as defined above for R9 and R11 ;

    p and q which can be identical or different are integers from 2 to 6; and

    r is zero or 1;

    when w is 3, A is one of the groups of the formula (VIa)-(VIc) ##STR66## in which R19, R22, R23, R24, R25, R26 and R28 which can be identical or different are as defined above for R9 and R11 ;

    R20 and R21 which can be identical or different are C2 -C12 alkylene or C4 -C12 alkylene interrupted by a group ##STR67## with R29 being defined as above for R15 ;

    s and v which can be identical or different are integers from 2 to 6;

    t is zero or 1;

    and R27 is C2 -C12 alkylene, andwhen w is 4,5 or 6, A is additionally a group of the formula (VII) ##STR68## in which R30 and R33 which can be identical or different are as defined above for R9 and R11 ;

    R31 and R32 which can be identical or different are C2 -C12 alkylene; and

    xi is 1, 2 or 3, and,when w is 4, A is also one of the groups of the formula (VIIIa)-(VIIIc) ##STR69## in which R34, R37, R38 and R41 which can be identical or different are as defined above for R9 and R11 ;

    R35, R36, R39 and R40 which can be identical or different are C2 -C12 alkylene;

    D1 is C2 -C12 alkylene, 2-hydroxytrimethylene, --CH2 CO--, xylylene or one of the groups of the formula (IXa) or (IXb) ##STR70## in which R43 is a direct bond, C1 -C12 alkylene, cyclohexylene or phenylene;

    R44 is as defined above for R8 ; and

    R42 is as defined above for R3 ; and

    when w is 6, A is also one of the groups of the formula (Xa)-(Xc) ##STR71## in which R45, R49, R50 and R53 which can be identical or different are as defined above for R9 and R11 ;

    R46, R47, R48, R51 and R52 which can be identical or different are C2 -C12 alkylene; and

    D2 is as defined above for D1.

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